CA2554047A1 - Derives d'alpha-aminoamide qui conviennent pour le traitement des troubles des voies urinaires inferieures - Google Patents

Derives d'alpha-aminoamide qui conviennent pour le traitement des troubles des voies urinaires inferieures Download PDF

Info

Publication number: CA2554047A1
Authority: CA; Canada
Prior art keywords: propanamide; dihydro; amino; benzylamino; ylmethyl
Prior art date: 2004-01-21
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002554047A

Other languages

English (en)

Inventor

Elena Barbanti

Orietta Veneroni

Florian Thaler

Roberto Pellicciari

Luca Benatti

Patricia Salvati

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Newron Pharmaceuticals SpA

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2004-01-21

Filing date

2005-01-20

Publication date

2005-08-04

2005-01-20 Application filed by Individual filed Critical Individual

2005-08-04 Publication of CA2554047A1 publication Critical patent/CA2554047A1/fr

Status Abandoned legal-status Critical Current

Links

208000026723 Urinary tract disease Diseases 0.000 title claims abstract description 15
208000014001 urinary system disease Diseases 0.000 title claims abstract description 15
238000011282 treatment Methods 0.000 title description 18
239000003814 drug Substances 0.000 claims abstract description 35
229940124597 therapeutic agent Drugs 0.000 claims abstract description 25
150000001875 compounds Chemical class 0.000 claims description 27
-1 3-Chlorobenzyloxy Chemical group 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 16
206010020853 Hypertonic bladder Diseases 0.000 claims description 15
208000009722 Overactive Urinary Bladder Diseases 0.000 claims description 15
208000020629 overactive bladder Diseases 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
206010046543 Urinary incontinence Diseases 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
BHJIBOFHEFDSAU-LBPRGKRZSA-N ralfinamide Chemical compound C1=CC(CN[C@@H](C)C(N)=O)=CC=C1OCC1=CC=CC=C1F BHJIBOFHEFDSAU-LBPRGKRZSA-N 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
201000007094 prostatitis Diseases 0.000 claims description 9
206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 8
208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 8
208000005615 Interstitial Cystitis Diseases 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
239000013543 active substance Substances 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
GOVNWFVCUCGMRC-UHFFFAOYSA-N n-methyl-2-[[3-(2-phenylethyl)-2,3-dihydro-1-benzofuran-5-yl]methylamino]propanamide Chemical compound C12=CC(CNC(C)C(=O)NC)=CC=C2OCC1CCC1=CC=CC=C1 GOVNWFVCUCGMRC-UHFFFAOYSA-N 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 4
ZFHZFSNDVRKNFJ-UHFFFAOYSA-N 2-[(3-benzyl-2,3-dihydro-1-benzofuran-5-yl)methylamino]-n-methylpropanamide Chemical compound C12=CC(CNC(C)C(=O)NC)=CC=C2OCC1CC1=CC=CC=C1 ZFHZFSNDVRKNFJ-UHFFFAOYSA-N 0.000 claims description 4
HCEHOTQIACBUFY-UHFFFAOYSA-N 2-[(3-benzyl-2,3-dihydro-1-benzofuran-5-yl)methylamino]propanamide Chemical compound C12=CC(CNC(C)C(N)=O)=CC=C2OCC1CC1=CC=CC=C1 HCEHOTQIACBUFY-UHFFFAOYSA-N 0.000 claims description 4
UKCXNYAVGSRSGD-UHFFFAOYSA-N 2-[(3-benzyl-2,3-dihydro-1-benzothiophen-5-yl)methylamino]propanamide Chemical compound C12=CC(CNC(C)C(N)=O)=CC=C2SCC1CC1=CC=CC=C1 UKCXNYAVGSRSGD-UHFFFAOYSA-N 0.000 claims description 4
FVPIWKJMLINOHB-UHFFFAOYSA-N 2-[(4-benzylsulfanylphenyl)methylamino]propanamide Chemical compound C1=CC(CNC(C)C(N)=O)=CC=C1SCC1=CC=CC=C1 FVPIWKJMLINOHB-UHFFFAOYSA-N 0.000 claims description 4
FIMOVVGRIMFVAD-UHFFFAOYSA-N 2-[[3-(2-phenylethyl)-2,3-dihydro-1-benzofuran-5-yl]methylamino]propanamide Chemical compound C12=CC(CNC(C)C(N)=O)=CC=C2OCC1CCC1=CC=CC=C1 FIMOVVGRIMFVAD-UHFFFAOYSA-N 0.000 claims description 4
BDJHWAWARIWBHG-UHFFFAOYSA-N 2-[[3-(2-phenylethyl)-2,3-dihydro-1-benzothiophen-5-yl]methylamino]propanamide Chemical compound C12=CC(CNC(C)C(N)=O)=CC=C2SCC1CCC1=CC=CC=C1 BDJHWAWARIWBHG-UHFFFAOYSA-N 0.000 claims description 4
KIKNVAARKWJZPA-UHFFFAOYSA-N 2-[[4-(2-phenylethyl)-2,3-dihydro-1-benzoxepin-7-yl]methylamino]propanamide Chemical compound C=1C2=CC(CNC(C)C(N)=O)=CC=C2OCCC=1CCC1=CC=CC=C1 KIKNVAARKWJZPA-UHFFFAOYSA-N 0.000 claims description 4
BHJIBOFHEFDSAU-UHFFFAOYSA-N 2-[[4-[(2-fluorophenyl)methoxy]phenyl]methylamino]propanamide Chemical compound C1=CC(CNC(C)C(N)=O)=CC=C1OCC1=CC=CC=C1F BHJIBOFHEFDSAU-UHFFFAOYSA-N 0.000 claims description 4
JEARPZLCKWXTFT-UHFFFAOYSA-N 2-[[4-[(3-fluorophenyl)methoxy]phenyl]methylamino]-2-methylpropanamide Chemical compound C1=CC(CNC(C)(C)C(N)=O)=CC=C1OCC1=CC=CC(F)=C1 JEARPZLCKWXTFT-UHFFFAOYSA-N 0.000 claims description 4
NEMGRZFTLSKBAP-UHFFFAOYSA-N 2-[[4-[(3-fluorophenyl)methoxy]phenyl]methylamino]propanamide Chemical compound C1=CC(CNC(C)C(N)=O)=CC=C1OCC1=CC=CC(F)=C1 NEMGRZFTLSKBAP-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
CTFCBIWUTVXAOP-UHFFFAOYSA-N 2-[[3-(2-phenylethyl)-3,4-dihydro-2h-chromen-6-yl]methylamino]propanamide Chemical compound C1C2=CC(CNC(C)C(N)=O)=CC=C2OCC1CCC1=CC=CC=C1 CTFCBIWUTVXAOP-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
PFZGGJTWPMATOE-HSZRJFAPSA-N (2r)-n-methyl-3-phenyl-2-[(4-phenylmethoxyphenyl)methylamino]propanamide Chemical compound C([C@H](C(=O)NC)NCC=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 PFZGGJTWPMATOE-HSZRJFAPSA-N 0.000 claims description 2
CNZVZXXYGVKPDE-KBXCAEBGSA-N (2r,3s)-3-hydroxy-n-methyl-2-[(4-phenylmethoxyphenyl)methylamino]butanamide Chemical compound C1=CC(CN[C@@H](C(=O)NC)[C@H](C)O)=CC=C1OCC1=CC=CC=C1 CNZVZXXYGVKPDE-KBXCAEBGSA-N 0.000 claims description 2
FVPIWKJMLINOHB-ZDUSSCGKSA-N (2s)-2-[(4-benzylsulfanylphenyl)methylamino]propanamide Chemical compound C1=CC(CN[C@@H](C)C(N)=O)=CC=C1SCC1=CC=CC=C1 FVPIWKJMLINOHB-ZDUSSCGKSA-N 0.000 claims description 2
XAIFSOMSPYROQW-LBPRGKRZSA-N (2s)-2-[[3-[(2-fluorophenyl)methoxy]phenyl]methylamino]propanamide Chemical compound NC(=O)[C@H](C)NCC1=CC=CC(OCC=2C(=CC=CC=2)F)=C1 XAIFSOMSPYROQW-LBPRGKRZSA-N 0.000 claims description 2
VONHEHWUTWRQCB-AWEZNQCLSA-N (2s)-2-[[4-(2-phenylethyl)phenyl]methylamino]propanamide Chemical compound C1=CC(CN[C@@H](C)C(N)=O)=CC=C1CCC1=CC=CC=C1 VONHEHWUTWRQCB-AWEZNQCLSA-N 0.000 claims description 2
AHMWTDOZNQOCAI-UHFFFAOYSA-N 2-(2-fluorophenyl)-2-[[4-[(2-fluorophenyl)methoxy]phenyl]methylamino]acetamide Chemical compound C=1C=CC=C(F)C=1C(C(=O)N)NCC(C=C1)=CC=C1OCC1=CC=CC=C1F AHMWTDOZNQOCAI-UHFFFAOYSA-N 0.000 claims description 2
SUAPKJRANCSCBZ-UHFFFAOYSA-N 2-(2-fluorophenyl)-2-[[4-[(3-fluorophenyl)methoxy]phenyl]methylamino]acetamide Chemical compound C=1C=CC=C(F)C=1C(C(=O)N)NCC(C=C1)=CC=C1OCC1=CC=CC(F)=C1 SUAPKJRANCSCBZ-UHFFFAOYSA-N 0.000 claims description 2
UZUNVRHFYYUUJH-UHFFFAOYSA-N 2-(3-fluorophenyl)-2-[[4-[(2-fluorophenyl)methoxy]phenyl]methylamino]acetamide Chemical compound C=1C=CC(F)=CC=1C(C(=O)N)NCC(C=C1)=CC=C1OCC1=CC=CC=C1F UZUNVRHFYYUUJH-UHFFFAOYSA-N 0.000 claims description 2
RBPLIQLNWOKJFW-UHFFFAOYSA-N 2-(3-fluorophenyl)-2-[[4-[(3-fluorophenyl)methoxy]phenyl]methylamino]acetamide Chemical compound C=1C=CC(F)=CC=1C(C(=O)N)NCC(C=C1)=CC=C1OCC1=CC=CC(F)=C1 RBPLIQLNWOKJFW-UHFFFAOYSA-N 0.000 claims description 2
JHQRDMZNCRDZIN-UHFFFAOYSA-N 2-[(3-phenylmethoxyphenyl)methylamino]propanamide Chemical compound NC(=O)C(C)NCC1=CC=CC(OCC=2C=CC=CC=2)=C1 JHQRDMZNCRDZIN-UHFFFAOYSA-N 0.000 claims description 2
IEHDKRBHKAGVKZ-UHFFFAOYSA-N 2-[(4-phenylmethoxyphenyl)methylamino]propanamide Chemical compound C1=CC(CNC(C)C(N)=O)=CC=C1OCC1=CC=CC=C1 IEHDKRBHKAGVKZ-UHFFFAOYSA-N 0.000 claims description 2
FAMQOOVSHKPIHZ-UHFFFAOYSA-N 2-[(4-thiophen-2-yloxyphenyl)methylamino]propanamide Chemical compound C1=CC(CNC(C)C(N)=O)=CC=C1OC1=CC=CS1 FAMQOOVSHKPIHZ-UHFFFAOYSA-N 0.000 claims description 2
BMPOJUVVLQGTSW-UHFFFAOYSA-N 2-[2-[4-[(3-chlorophenyl)methoxy]phenyl]ethylamino]propanamide Chemical compound C1=CC(CCNC(C)C(N)=O)=CC=C1OCC1=CC=CC(Cl)=C1 BMPOJUVVLQGTSW-UHFFFAOYSA-N 0.000 claims description 2
XAIFSOMSPYROQW-UHFFFAOYSA-N 2-[[3-[(2-fluorophenyl)methoxy]phenyl]methylamino]propanamide Chemical compound NC(=O)C(C)NCC1=CC=CC(OCC=2C(=CC=CC=2)F)=C1 XAIFSOMSPYROQW-UHFFFAOYSA-N 0.000 claims description 2
XZVNPHMSKCAJKA-UHFFFAOYSA-N 2-[[3-[(3-fluorophenyl)methoxy]phenyl]methylamino]propanamide Chemical compound NC(=O)C(C)NCC1=CC=CC(OCC=2C=C(F)C=CC=2)=C1 XZVNPHMSKCAJKA-UHFFFAOYSA-N 0.000 claims description 2
VONHEHWUTWRQCB-UHFFFAOYSA-N 2-[[4-(2-phenylethyl)phenyl]methylamino]propanamide Chemical compound C1=CC(CNC(C)C(N)=O)=CC=C1CCC1=CC=CC=C1 VONHEHWUTWRQCB-UHFFFAOYSA-N 0.000 claims description 2
KYGCCDPEFAOIFA-UHFFFAOYSA-N 2-[[4-(3-phenylpropoxy)phenyl]methylamino]propanamide Chemical compound C1=CC(CNC(C)C(N)=O)=CC=C1OCCCC1=CC=CC=C1 KYGCCDPEFAOIFA-UHFFFAOYSA-N 0.000 claims description 2
DWHVPAYXTBJTSK-UHFFFAOYSA-N 2-[[4-(4-phenylbutoxy)phenyl]methylamino]propanamide Chemical compound C1=CC(CNC(C)C(N)=O)=CC=C1OCCCCC1=CC=CC=C1 DWHVPAYXTBJTSK-UHFFFAOYSA-N 0.000 claims description 2
OMSNFOXNGYYQRI-UHFFFAOYSA-N 2-[[4-(5-phenylpentoxy)phenyl]methylamino]propanamide Chemical compound C1=CC(CNC(C)C(N)=O)=CC=C1OCCCCCC1=CC=CC=C1 OMSNFOXNGYYQRI-UHFFFAOYSA-N 0.000 claims description 2
JCIZOFILWMNHSB-UHFFFAOYSA-N 2-[[4-[(2-chlorophenyl)methoxy]phenyl]methylamino]-3-hydroxy-n-methylpropanamide Chemical compound C1=CC(CNC(CO)C(=O)NC)=CC=C1OCC1=CC=CC=C1Cl JCIZOFILWMNHSB-UHFFFAOYSA-N 0.000 claims description 2
QWRXERHYJYREES-UHFFFAOYSA-N 2-[[4-[(2-chlorophenyl)methoxy]phenyl]methylamino]propanamide Chemical compound C1=CC(CNC(C)C(N)=O)=CC=C1OCC1=CC=CC=C1Cl QWRXERHYJYREES-UHFFFAOYSA-N 0.000 claims description 2
JYXHMCQBDXKJFB-UHFFFAOYSA-N 2-[[4-[(2-fluorophenyl)methoxy]phenyl]methyl-methylamino]-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(C(N)=O)N(C)CC(C=C1)=CC=C1OCC1=CC=CC=C1F JYXHMCQBDXKJFB-UHFFFAOYSA-N 0.000 claims description 2
ARKJBLYSUDCWBM-UHFFFAOYSA-N 2-[[4-[(2-fluorophenyl)methoxy]phenyl]methylamino]-2-methylpropanamide Chemical compound C1=CC(CNC(C)(C)C(N)=O)=CC=C1OCC1=CC=CC=C1F ARKJBLYSUDCWBM-UHFFFAOYSA-N 0.000 claims description 2
KWMDBCXQGPZBCB-UHFFFAOYSA-N 2-[[4-[(2-fluorophenyl)methoxy]phenyl]methylamino]-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(C(=O)N)NCC(C=C1)=CC=C1OCC1=CC=CC=C1F KWMDBCXQGPZBCB-UHFFFAOYSA-N 0.000 claims description 2
ALWXTQNAGVDEMX-UHFFFAOYSA-N 2-[[4-[(2-fluorophenyl)methoxy]phenyl]methylamino]-3-hydroxy-n-methylpropanamide Chemical compound C1=CC(CNC(CO)C(=O)NC)=CC=C1OCC1=CC=CC=C1F ALWXTQNAGVDEMX-UHFFFAOYSA-N 0.000 claims description 2
HYRAJPATCBQKCF-UHFFFAOYSA-N 2-[[4-[(2-fluorophenyl)methoxy]phenyl]methylamino]-3-hydroxypropanamide Chemical compound C1=CC(CNC(CO)C(=O)N)=CC=C1OCC1=CC=CC=C1F HYRAJPATCBQKCF-UHFFFAOYSA-N 0.000 claims description 2
WGXNRJBCPJAUOL-UHFFFAOYSA-N 2-[[4-[(2-fluorophenyl)methoxy]phenyl]methylamino]-n-methylpropanamide Chemical compound C1=CC(CNC(C)C(=O)NC)=CC=C1OCC1=CC=CC=C1F WGXNRJBCPJAUOL-UHFFFAOYSA-N 0.000 claims description 2
CXWAISQTEMSTKD-UHFFFAOYSA-N 2-[[4-[(2-fluorophenyl)methylsulfanyl]phenyl]methylamino]propanamide Chemical compound C1=CC(CNC(C)C(N)=O)=CC=C1SCC1=CC=CC=C1F CXWAISQTEMSTKD-UHFFFAOYSA-N 0.000 claims description 2
OBIIMYCBFFXWQB-UHFFFAOYSA-N 2-[[4-[(2-methoxyphenyl)methoxy]phenyl]methylamino]propanamide Chemical compound COC1=CC=CC=C1COC1=CC=C(CNC(C)C(N)=O)C=C1 OBIIMYCBFFXWQB-UHFFFAOYSA-N 0.000 claims description 2
MODFUWXCNUBNKW-UHFFFAOYSA-N 2-[[4-[(3-chlorophenyl)methoxy]phenyl]methylamino]-2-(3-fluorophenyl)acetamide Chemical compound C=1C=CC(F)=CC=1C(C(=O)N)NCC(C=C1)=CC=C1OCC1=CC=CC(Cl)=C1 MODFUWXCNUBNKW-UHFFFAOYSA-N 0.000 claims description 2
UGAZPYAMTAVKDF-UHFFFAOYSA-N 2-[[4-[(3-chlorophenyl)methoxy]phenyl]methylamino]-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(C(=O)N)NCC(C=C1)=CC=C1OCC1=CC=CC(Cl)=C1 UGAZPYAMTAVKDF-UHFFFAOYSA-N 0.000 claims description 2
JFADNUHMEURSIM-UHFFFAOYSA-N 2-[[4-[(3-chlorophenyl)methoxy]phenyl]methylamino]propanamide Chemical compound C1=CC(CNC(C)C(N)=O)=CC=C1OCC1=CC=CC(Cl)=C1 JFADNUHMEURSIM-UHFFFAOYSA-N 0.000 claims description 2
XWCJJIVVFMWOQA-UHFFFAOYSA-N 2-[[4-[(3-cyanophenyl)methoxy]phenyl]methylamino]-3-hydroxy-n,2-dimethylpropanamide Chemical compound C1=CC(CNC(C)(CO)C(=O)NC)=CC=C1OCC1=CC=CC(C#N)=C1 XWCJJIVVFMWOQA-UHFFFAOYSA-N 0.000 claims description 2
QNGQPQCXSOZZQG-UHFFFAOYSA-N 2-[[4-[(3-cyanophenyl)methoxy]phenyl]methylamino]-3-hydroxy-n-methylpropanamide Chemical compound C1=CC(CNC(CO)C(=O)NC)=CC=C1OCC1=CC=CC(C#N)=C1 QNGQPQCXSOZZQG-UHFFFAOYSA-N 0.000 claims description 2
BBMKDZGTJLFKTA-UHFFFAOYSA-N 2-[[4-[(3-cyanophenyl)methoxy]phenyl]methylamino]propanamide Chemical compound C1=CC(CNC(C)C(N)=O)=CC=C1OCC1=CC=CC(C#N)=C1 BBMKDZGTJLFKTA-UHFFFAOYSA-N 0.000 claims description 2
CYZUAXYGTDLCAW-UHFFFAOYSA-N 2-[[4-[(3-fluorophenyl)methoxy]phenyl]methyl-methylamino]-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(C(N)=O)N(C)CC(C=C1)=CC=C1OCC1=CC=CC(F)=C1 CYZUAXYGTDLCAW-UHFFFAOYSA-N 0.000 claims description 2
HCSMEIBTXUDXFF-UHFFFAOYSA-N 2-[[4-[(3-fluorophenyl)methoxy]phenyl]methylamino]-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(C(=O)N)NCC(C=C1)=CC=C1OCC1=CC=CC(F)=C1 HCSMEIBTXUDXFF-UHFFFAOYSA-N 0.000 claims description 2
HAQWBSZODRWECB-UHFFFAOYSA-N 2-[[4-[(3-fluorophenyl)methoxy]phenyl]methylamino]-3-hydroxy-n-methylpropanamide Chemical compound C1=CC(CNC(CO)C(=O)NC)=CC=C1OCC1=CC=CC(F)=C1 HAQWBSZODRWECB-UHFFFAOYSA-N 0.000 claims description 2
UTIKAYGNKRMHTP-UHFFFAOYSA-N 2-[[4-[(3-fluorophenyl)methoxy]phenyl]methylamino]-3-hydroxypropanamide Chemical compound C1=CC(CNC(CO)C(=O)N)=CC=C1OCC1=CC=CC(F)=C1 UTIKAYGNKRMHTP-UHFFFAOYSA-N 0.000 claims description 2
RLHPBZNGBNCVBL-UHFFFAOYSA-N 2-[[4-[(3-fluorophenyl)methoxy]phenyl]methylamino]-n-methylpropanamide Chemical compound C1=CC(CNC(C)C(=O)NC)=CC=C1OCC1=CC=CC(F)=C1 RLHPBZNGBNCVBL-UHFFFAOYSA-N 0.000 claims description 2
FZSPWFMNPPFIJE-UHFFFAOYSA-N 2-[[4-[(3-fluorophenyl)methylsulfanyl]phenyl]methylamino]propanamide Chemical compound C1=CC(CNC(C)C(N)=O)=CC=C1SCC1=CC=CC(F)=C1 FZSPWFMNPPFIJE-UHFFFAOYSA-N 0.000 claims description 2
JNSHSOGWMMBDOW-UHFFFAOYSA-N 2-[[4-[(3-methoxyphenyl)methoxy]phenyl]methylamino]propanamide Chemical compound COC1=CC=CC(COC=2C=CC(CNC(C)C(N)=O)=CC=2)=C1 JNSHSOGWMMBDOW-UHFFFAOYSA-N 0.000 claims description 2
KAWCXZXQTSSDOQ-UHFFFAOYSA-N 2-[[4-[(4-fluorophenyl)methoxy]phenyl]methylamino]propanamide Chemical compound C1=CC(CNC(C)C(N)=O)=CC=C1OCC1=CC=C(F)C=C1 KAWCXZXQTSSDOQ-UHFFFAOYSA-N 0.000 claims description 2
DABZEFFZGNRXOC-UHFFFAOYSA-N 2-[methyl-[(4-phenylmethoxyphenyl)methyl]amino]propanamide Chemical compound C1=CC(CN(C)C(C)C(N)=O)=CC=C1OCC1=CC=CC=C1 DABZEFFZGNRXOC-UHFFFAOYSA-N 0.000 claims description 2
AROJRYZKACVPEC-UHFFFAOYSA-N 2-phenyl-2-[(4-phenylmethoxyphenyl)methylamino]acetamide Chemical compound C=1C=CC=CC=1C(C(=O)N)NCC(C=C1)=CC=C1OCC1=CC=CC=C1 AROJRYZKACVPEC-UHFFFAOYSA-N 0.000 claims description 2
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 2
JMIJOQDPXHRPOI-UHFFFAOYSA-N 3-hydroxy-2-[(4-phenylmethoxyphenyl)methylamino]propanamide Chemical compound C1=CC(CNC(CO)C(=O)N)=CC=C1OCC1=CC=CC=C1 JMIJOQDPXHRPOI-UHFFFAOYSA-N 0.000 claims description 2
CNZVZXXYGVKPDE-UHFFFAOYSA-N 3-hydroxy-n-methyl-2-[(4-phenylmethoxyphenyl)methylamino]butanamide Chemical compound C1=CC(CNC(C(=O)NC)C(C)O)=CC=C1OCC1=CC=CC=C1 CNZVZXXYGVKPDE-UHFFFAOYSA-N 0.000 claims description 2
PPNQCSNKEHUNCF-UHFFFAOYSA-N 3-hydroxy-n-methyl-2-[(4-phenylmethoxyphenyl)methylamino]propanamide Chemical compound C1=CC(CNC(CO)C(=O)NC)=CC=C1OCC1=CC=CC=C1 PPNQCSNKEHUNCF-UHFFFAOYSA-N 0.000 claims description 2
HXJYSYZXIYIPLJ-UHFFFAOYSA-N n,3-dimethyl-2-[(4-phenylmethoxyphenyl)methylamino]butanamide Chemical compound C1=CC(CNC(C(=O)NC)C(C)C)=CC=C1OCC1=CC=CC=C1 HXJYSYZXIYIPLJ-UHFFFAOYSA-N 0.000 claims description 2
PFZGGJTWPMATOE-UHFFFAOYSA-N n-methyl-3-phenyl-2-[(4-phenylmethoxyphenyl)methylamino]propanamide Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1CNC(C(=O)NC)CC1=CC=CC=C1 PFZGGJTWPMATOE-UHFFFAOYSA-N 0.000 claims description 2
NEMGRZFTLSKBAP-LBPRGKRZSA-N safinamide Chemical compound C1=CC(CN[C@@H](C)C(N)=O)=CC=C1OCC1=CC=CC(F)=C1 NEMGRZFTLSKBAP-LBPRGKRZSA-N 0.000 claims description 2
XZVNPHMSKCAJKA-LBPRGKRZSA-N (2s)-2-[[3-[(3-fluorophenyl)methoxy]phenyl]methylamino]propanamide Chemical compound NC(=O)[C@H](C)NCC1=CC=CC(OCC=2C=C(F)C=CC=2)=C1 XZVNPHMSKCAJKA-LBPRGKRZSA-N 0.000 claims 1
WGXNRJBCPJAUOL-ZDUSSCGKSA-N (2s)-2-[[4-[(2-fluorophenyl)methoxy]phenyl]methylamino]-n-methylpropanamide Chemical compound C1=CC(CN[C@@H](C)C(=O)NC)=CC=C1OCC1=CC=CC=C1F WGXNRJBCPJAUOL-ZDUSSCGKSA-N 0.000 claims 1
RLHPBZNGBNCVBL-ZDUSSCGKSA-N (2s)-2-[[4-[(3-fluorophenyl)methoxy]phenyl]methylamino]-n-methylpropanamide Chemical compound C1=CC(CN[C@@H](C)C(=O)NC)=CC=C1OCC1=CC=CC(F)=C1 RLHPBZNGBNCVBL-ZDUSSCGKSA-N 0.000 claims 1
MBABTXVDELKRJL-UHFFFAOYSA-N 2-[[4-[2-(3-fluorophenyl)ethoxy]phenyl]methylamino]propanamide Chemical compound C1=CC(CNC(C)C(N)=O)=CC=C1OCCC1=CC=CC(F)=C1 MBABTXVDELKRJL-UHFFFAOYSA-N 0.000 claims 1
FMVVWKBPYPEPAF-UHFFFAOYSA-N 2-[[4-[2-(3-fluorophenyl)ethyl]phenyl]methylamino]propanamide Chemical compound C1=CC(CNC(C)C(N)=O)=CC=C1CCC1=CC=CC(F)=C1 FMVVWKBPYPEPAF-UHFFFAOYSA-N 0.000 claims 1
230000007170 pathology Effects 0.000 claims 1
238000000034 method Methods 0.000 abstract description 9
230000000694 effects Effects 0.000 abstract description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
210000003932 urinary bladder Anatomy 0.000 description 16
101150041968 CDC13 gene Proteins 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
239000000243 solution Substances 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
238000005160 1H NMR spectroscopy Methods 0.000 description 10
208000035475 disorder Diseases 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
229940079593 drug Drugs 0.000 description 7
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
241000124008 Mammalia Species 0.000 description 6
241000700159 Rattus Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229960004397 cyclophosphamide Drugs 0.000 description 6
238000001802 infusion Methods 0.000 description 6
210000002307 prostate Anatomy 0.000 description 6
239000000725 suspension Substances 0.000 description 6
208000024891 symptom Diseases 0.000 description 6
210000002700 urine Anatomy 0.000 description 6
206010005052 Bladder irritation Diseases 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
238000002648 combination therapy Methods 0.000 description 5
201000010099 disease Diseases 0.000 description 5
238000003818 flash chromatography Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 4
230000009286 beneficial effect Effects 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
238000010253 intravenous injection Methods 0.000 description 4
230000036453 micturition reflex Effects 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
230000009467 reduction Effects 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
206010037211 Psychomotor hyperactivity Diseases 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
229930006000 Sucrose Natural products 0.000 description 3
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
230000001154 acute effect Effects 0.000 description 3
239000012300 argon atmosphere Substances 0.000 description 3
235000013681 dietary sucrose Nutrition 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
230000004968 inflammatory condition Effects 0.000 description 3
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
230000000926 neurological effect Effects 0.000 description 3
206010029446 nocturia Diseases 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
229960004793 sucrose Drugs 0.000 description 3
239000000829 suppository Substances 0.000 description 3
238000001356 surgical procedure Methods 0.000 description 3
239000003826 tablet Substances 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
210000001635 urinary tract Anatomy 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
XRCLJRMJQWBION-UHFFFAOYSA-N (3-benzyl-2,3-dihydro-1-benzofuran-5-yl)methanol Chemical compound C12=CC(CO)=CC=C2OCC1CC1=CC=CC=C1 XRCLJRMJQWBION-UHFFFAOYSA-N 0.000 description 2
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
YAIQLSGJDFUANQ-UHFFFAOYSA-N 2-(benzylamino)propanamide Chemical class NC(=O)C(C)NCC1=CC=CC=C1 YAIQLSGJDFUANQ-UHFFFAOYSA-N 0.000 description 2
YHAFDUCDNIGHAB-UHFFFAOYSA-N 3-(2-phenylethyl)-2,3-dihydro-1-benzofuran-5-carbaldehyde Chemical compound C12=CC(C=O)=CC=C2OCC1CCC1=CC=CC=C1 YHAFDUCDNIGHAB-UHFFFAOYSA-N 0.000 description 2
QXCMYTNVJPRKFB-UHFFFAOYSA-N 3-benzyl-2,3-dihydro-1-benzofuran-5-carboxylic acid Chemical class C12=CC(C(=O)O)=CC=C2OCC1CC1=CC=CC=C1 QXCMYTNVJPRKFB-UHFFFAOYSA-N 0.000 description 2
DIVZZNDPQLODQB-UHFFFAOYSA-N 4-bromobut-2-enylbenzene Chemical class BrCC=CCC1=CC=CC=C1 DIVZZNDPQLODQB-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
208000035143 Bacterial infection Diseases 0.000 description 2
206010069918 Bacterial prostatitis Diseases 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
206010021639 Incontinence Diseases 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
208000002193 Pain Diseases 0.000 description 2
108010052164 Sodium Channels Proteins 0.000 description 2
102000018674 Sodium Channels Human genes 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
KKLXEHOEFQIODK-UHFFFAOYSA-N [3-(2-phenylethyl)-2,3-dihydro-1-benzofuran-5-yl]methanol Chemical compound C12=CC(CO)=CC=C2OCC1CCC1=CC=CC=C1 KKLXEHOEFQIODK-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
210000003766 afferent neuron Anatomy 0.000 description 2
235000010443 alginic acid Nutrition 0.000 description 2
229920000615 alginic acid Polymers 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000001961 anticonvulsive agent Substances 0.000 description 2
208000022362 bacterial infectious disease Diseases 0.000 description 2
230000008901 benefit Effects 0.000 description 2
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
229940105329 carboxymethylcellulose Drugs 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
230000001684 chronic effect Effects 0.000 description 2
230000008602 contraction Effects 0.000 description 2
230000006378 damage Effects 0.000 description 2
235000005911 diet Nutrition 0.000 description 2
230000037213 diet Effects 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
206010013990 dysuria Diseases 0.000 description 2
MOZKYYWKSSZUMP-UHFFFAOYSA-N ethyl 3-(2-phenylethyl)-2,3-dihydro-1-benzofuran-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2OCC1CCC1=CC=CC=C1 MOZKYYWKSSZUMP-UHFFFAOYSA-N 0.000 description 2
IWQRPHOZQILUHZ-UHFFFAOYSA-N ethyl 3-benzyl-2,3-dihydro-1-benzofuran-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2OCC1CC1=CC=CC=C1 IWQRPHOZQILUHZ-UHFFFAOYSA-N 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
238000010255 intramuscular injection Methods 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000010410 layer Substances 0.000 description 2
235000010445 lecithin Nutrition 0.000 description 2
239000000787 lecithin Substances 0.000 description 2
229940067606 lecithin Drugs 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
239000000463 material Substances 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
230000027939 micturition Effects 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
230000001272 neurogenic effect Effects 0.000 description 2
230000001734 parasympathetic effect Effects 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000013223 sprague-dawley female rat Methods 0.000 description 2
239000008107 starch Substances 0.000 description 2
229940032147 starch Drugs 0.000 description 2
239000008223 sterile water Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 2
210000003708 urethra Anatomy 0.000 description 2
238000009736 wetting Methods 0.000 description 2
UHWFDFLWTAIHRE-DFWYDOINSA-N (2s)-2-amino-n-methylpropanamide;hydrochloride Chemical compound Cl.CNC(=O)[C@H](C)N UHWFDFLWTAIHRE-DFWYDOINSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 1
UFLBPQQRWQTTQC-UHFFFAOYSA-N 3-(2-phenylethyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid Chemical class C12=CC(C(=O)O)=CC=C2OCC1CCC1=CC=CC=C1 UFLBPQQRWQTTQC-UHFFFAOYSA-N 0.000 description 1
CYIQNPRKSVDNCS-UHFFFAOYSA-N 3-benzyl-2,3-dihydro-1-benzofuran-5-carbaldehyde Chemical compound C12=CC(C=O)=CC=C2OCC1CC1=CC=CC=C1 CYIQNPRKSVDNCS-UHFFFAOYSA-N 0.000 description 1
NXMXURLEDVYQRT-SNAWJCMRSA-N 3-iodo-4-[(E)-4-phenylbut-2-enoxy]benzoic acid Chemical compound IC1=CC(C(=O)O)=CC=C1OC\C=C\CC1=CC=CC=C1 NXMXURLEDVYQRT-SNAWJCMRSA-N 0.000 description 1
FYXSNIFXNFLBLO-UHFFFAOYSA-N 3-iodo-4-sulfanylbenzoic acid Chemical class OC(=O)C1=CC=C(S)C(I)=C1 FYXSNIFXNFLBLO-UHFFFAOYSA-N 0.000 description 1
BJZXBZGGLXHODK-UHFFFAOYSA-N 4-hydroxy-3-iodobenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(I)=C1 BJZXBZGGLXHODK-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
206010056948 Automatic bladder Diseases 0.000 description 1
206010071445 Bladder outlet obstruction Diseases 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
108091006146 Channels Proteins 0.000 description 1
206010056874 Chemical cystitis Diseases 0.000 description 1
206010010305 Confusional state Diseases 0.000 description 1
206010010774 Constipation Diseases 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
229920000858 Cyclodextrin Polymers 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
208000003556 Dry Eye Syndromes Diseases 0.000 description 1
206010013774 Dry eye Diseases 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
206010020880 Hypertrophy Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
206010065390 Inflammatory pain Diseases 0.000 description 1
108090000862 Ion Channels Proteins 0.000 description 1
102000004310 Ion Channels Human genes 0.000 description 1
206010071289 Lower urinary tract symptoms Diseases 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
208000029578 Muscle disease Diseases 0.000 description 1
BWCJIXDHUGCDIE-IMECTCCJSA-N NC(=O)[C@H](C)NCC1=CC=CC(OCC=2C=C(F)C=CC=2)=C1.C1=CC(CN[C@@H](C)C(=O)NC)=CC=C1OCC1=CC=CC=C1F Chemical compound NC(=O)[C@H](C)NCC1=CC=CC(OCC=2C=C(F)C=CC=2)=C1.C1=CC(CN[C@@H](C)C(=O)NC)=CC=C1OCC1=CC=CC=C1F BWCJIXDHUGCDIE-IMECTCCJSA-N 0.000 description 1
206010033557 Palpitations Diseases 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
208000000450 Pelvic Pain Diseases 0.000 description 1
206010064229 Pelvic discomfort Diseases 0.000 description 1
206010036018 Pollakiuria Diseases 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
206010041349 Somnolence Diseases 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
208000006011 Stroke Diseases 0.000 description 1
229940123445 Tricyclic antidepressant Drugs 0.000 description 1
208000006568 Urinary Bladder Calculi Diseases 0.000 description 1
208000003800 Urinary Bladder Neck Obstruction Diseases 0.000 description 1
206010046555 Urinary retention Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
LUXUAZKGQZPOBZ-SAXJAHGMSA-N [(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (Z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O LUXUAZKGQZPOBZ-SAXJAHGMSA-N 0.000 description 1
230000003187 abdominal effect Effects 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000036982 action potential Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000000674 adrenergic antagonist Substances 0.000 description 1
OQIQSTLJSLGHID-WNWIJWBNSA-N aflatoxin B1 Chemical group C=1([C@@H]2C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O OQIQSTLJSLGHID-WNWIJWBNSA-N 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000004075 alteration Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000009167 androgen deprivation therapy Methods 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000003574 anti-allodynic effect Effects 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
230000001430 anti-depressive effect Effects 0.000 description 1
230000003556 anti-epileptic effect Effects 0.000 description 1
230000001022 anti-muscarinic effect Effects 0.000 description 1
230000000648 anti-parkinson Effects 0.000 description 1
230000001663 anti-spastic effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
239000000939 antiparkinson agent Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
210000003403 autonomic nervous system Anatomy 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
150000004802 benzothiophens Chemical class 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
230000001010 compromised effect Effects 0.000 description 1
238000012790 confirmation Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
150000001907 coumarones Chemical class 0.000 description 1
229940111134 coxibs Drugs 0.000 description 1
238000011262 co‐therapy Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
229940097362 cyclodextrins Drugs 0.000 description 1
239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
201000003146 cystitis Diseases 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000008298 dragée Substances 0.000 description 1
206010013781 dry mouth Diseases 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000009505 enteric coating Methods 0.000 description 1
239000002702 enteric coating Substances 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
HOAXKZYYZXASLJ-UHFFFAOYSA-N ethyl 4-hydroxy-3-iodobenzoate Chemical compound CCOC(=O)C1=CC=C(O)C(I)=C1 HOAXKZYYZXASLJ-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000007941 film coated tablet Substances 0.000 description 1
239000007888 film coating Substances 0.000 description 1
238000009501 film coating Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000000499 gel Substances 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000036541 health Effects 0.000 description 1
230000003054 hormonal effect Effects 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
208000013403 hyperactivity Diseases 0.000 description 1
230000009610 hypersensitivity Effects 0.000 description 1
239000003326 hypnotic agent Substances 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
239000012678 infectious agent Substances 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
208000014674 injury Diseases 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
230000036724 intravesical pressure Effects 0.000 description 1
239000002085 irritant Substances 0.000 description 1
231100000021 irritant Toxicity 0.000 description 1
230000003902 lesion Effects 0.000 description 1
229960004393 lidocaine hydrochloride Drugs 0.000 description 1
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
230000003211 malignant effect Effects 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
239000003887 narcotic antagonist Substances 0.000 description 1
229920001206 natural gum Polymers 0.000 description 1
208000004296 neuralgia Diseases 0.000 description 1
208000021722 neuropathic pain Diseases 0.000 description 1
230000000324 neuroprotective effect Effects 0.000 description 1
238000013546 non-drug therapy Methods 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000001814 pectin Substances 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229940043138 pentosan polysulfate Drugs 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
208000033808 peripheral neuropathy Diseases 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229940068965 polysorbates Drugs 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000000063 preceeding effect Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000008569 process Effects 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000011552 rat model Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000011514 reflex Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
150000003870 salicylic acids Chemical class 0.000 description 1
230000001953 sensory effect Effects 0.000 description 1
210000001044 sensory neuron Anatomy 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000009097 single-agent therapy Methods 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
239000003195 sodium channel blocking agent Substances 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000002889 sympathetic effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000012549 training Methods 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
239000003029 tricyclic antidepressant agent Substances 0.000 description 1
208000022934 urinary frequency Diseases 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
230000036318 urination frequency Effects 0.000 description 1
210000001215 vagina Anatomy 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
- A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/28—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/58—Radicals substituted by nitrogen atoms

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Urology & Nephrology (AREA)
Pain & Pain Management (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Furan Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA002554047A 2004-01-21 2005-01-20 Derives d'alpha-aminoamide qui conviennent pour le traitement des troubles des voies urinaires inferieures Abandoned CA2554047A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP04001175A EP1557166A1 (fr)	2004-01-21	2004-01-21	Derives d'alpha-aminoamides pour le traitement des désordres de l'appareil urinaire inférieur
EP04001175.1		2004-01-21
PCT/EP2005/000514 WO2005070405A1 (fr)	2004-01-21	2005-01-20	Derives d'alpha-aminoamide qui conviennent pour le traitement des troubles des voies urinaires inferieures

Publications (1)

Publication Number	Publication Date
CA2554047A1 true CA2554047A1 (fr)	2005-08-04

Family

ID=34626470

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002554047A Abandoned CA2554047A1 (fr)	2004-01-21	2005-01-20	Derives d'alpha-aminoamide qui conviennent pour le traitement des troubles des voies urinaires inferieures

Country Status (14)

Country	Link
US (1)	US7718815B2 (fr)
EP (1)	EP1557166A1 (fr)
JP (1)	JP2007518763A (fr)
KR (1)	KR101310882B1 (fr)
CN (1)	CN100584323C (fr)
AU (1)	AU2005205903B2 (fr)
BR (1)	BRPI0506970B8 (fr)
CA (1)	CA2554047A1 (fr)
IL (1)	IL176968A (fr)
NO (1)	NO20063368L (fr)
NZ (1)	NZ548638A (fr)
PL (1)	PL380825A1 (fr)
RU (1)	RU2395504C2 (fr)
WO (1)	WO2005070405A1 (fr)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2363983A (en) *	2000-06-29	2002-01-16	Hunter Fleming Ltd	Protection against neuronal damage using 7-hydroxyepiandrosterone
US20080096965A1 (en) *	2004-09-10	2008-04-24	Newron Pharmaceuticals S.P.A.	(Halobenzyloxy) Benzylamino-Propanamides as Sodium and/or Calcium Channel Selective Modulators
MY145694A (en)	2005-04-11	2012-03-30	Xenon Pharmaceuticals Inc	Spiroheterocyclic compounds and their uses as therapeutic agents
AR056968A1 (es)	2005-04-11	2007-11-07	Xenon Pharmaceuticals Inc	Compuestos espiro-oxindol y composiciones farmacéuticas
WO2007002885A2 (fr) *	2005-06-29	2007-01-04	University Of Virginia Patent Foundation	Compositions et procedes pour utiliser un agent de blocage du canal sodique
EP1963280B1 (fr) *	2005-12-22	2015-10-28	Newron Pharmaceuticals S.p.A.	Dérivés 2-phényléthylamino comme modulateurs des canaux de calcium et/ou sodium
DK2474521T3 (en)	2006-06-19	2016-10-31	Newron Pharm Spa	High-purity 2- [4- (3- and 2-fluorobenzyloxy) benzylamino] propanamides for use as pharmaceuticals and pharmaceutical formulations thus
WO2008046087A2 (fr) *	2006-10-12	2008-04-17	Xenon Pharmaceuticals Inc.	Composés spiro et leurs utilisations en tant qu'agents thérapeutiques
AR063280A1 (es)	2006-10-12	2009-01-21	Xenon Pharmaceuticals Inc	Uso de compuestos de espiro-oxindol como agentes terapeuticos
DK2155663T3 (en)	2007-06-15	2018-01-22	Newron Pharm Spa	SUBSTITUTED 2- [2- (PHENYL) ETHYLAMINO] ALKANAMIDE DERIVATIVES AND THEIR USE AS SODIUM AND / OR CALCIUM CHANNEL MODULATORS
KR101593627B1 (ko)	2007-12-11	2016-02-11	뉴론 파마슈티칼즈 에스. 피. 에이.	고순도의 ２［４（３ 또는 ２플루오로벤질옥시）벤질아미노］프로판아미드의 제조방법
CN105218565A (zh)	2008-10-17	2016-01-06	泽农医药公司	螺羟吲哚化合物及其作为治疗剂的用途
WO2010045197A1 (fr)	2008-10-17	2010-04-22	Xenon Pharmaceuticals, Inc.	Composés spiro-oxindole et leur utilisation comme agents thérapeutiques
AR077252A1 (es)	2009-06-29	2011-08-10	Xenon Pharmaceuticals Inc	Enantiomeros de compuestos de espirooxindol y sus usos como agentes terapeuticos
CN102753556B (zh)	2009-10-14	2015-05-13	泽农医药公司	螺-羟吲哚化合物的合成方法
NZ601667A (en)	2010-02-26	2014-10-31	Xenon Pharmaceuticals Inc	Pharmaceutical compositions of spiro-oxindole compound for topical administration and their use as therapeutic agents
NZ602648A (en)	2010-04-27	2014-10-31	Newron Pharm Spa	Process for the production of ralfinamide methanesulfonate salts or their r-enantiomers
TW201636017A (zh)	2015-02-05	2016-10-16	梯瓦製藥國際有限責任公司	以螺吲哚酮化合物之局部調配物治療帶狀疱疹後遺神經痛之方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL94466A (en) *	1989-05-25	1995-01-24	Erba Carlo Spa	Pharmaceutical preparations containing the history of A-amino carboxamide N-phenylalkyl are converted into such new compounds and their preparation
AU717598B2 (en) *	1995-03-10	2000-03-30	G.D. Searle & Co.	Heterocyclecarbonyl amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
GB9515412D0 (en) *	1995-07-27	1995-09-27	Pharmacia Spa	2-(4-substituted)-benzylamino-2-methyl-propanamide derivatives
ES2352739T3 (es) *	1997-11-21	2011-02-22	Purdue Neuroscience Company	2-aminoacetamidas sustituidas y el uso de las mismas.
GB9727523D0 (en) *	1997-12-31	1998-02-25	Pharmacia & Upjohn Spa	Alpha-aminoamide derivatives useful as analgesic agents
SI1423168T1 (sl) *	2001-09-03	2006-06-30	Newron Pharm Spa	Farmacevtski sestavek, ki vsebuje gabapentin ali njegov analog in alfa-aminoamid, in njegova analgetska uporaba
US20040209960A1 (en)	2003-01-30	2004-10-21	Dynogen Pharmaceuticals, Inc.	Methods of treating lower urinary tract disorders using sodium channell modulators
ES2339021T3 (es)	2003-08-25	2010-05-14	Newron Pharmaceuticals S.P.A.	Derivados de alfa-aminoamida utiles como agentes antiinflamatorios.

2004
- 2004-01-21 EP EP04001175A patent/EP1557166A1/fr not_active Withdrawn
2005
- 2005-01-20 WO PCT/EP2005/000514 patent/WO2005070405A1/fr not_active Ceased
- 2005-01-20 CN CN200580002785A patent/CN100584323C/zh not_active Expired - Lifetime
- 2005-01-20 NZ NZ548638A patent/NZ548638A/en not_active IP Right Cessation
- 2005-01-20 PL PL380825A patent/PL380825A1/pl not_active Application Discontinuation
- 2005-01-20 AU AU2005205903A patent/AU2005205903B2/en not_active Expired
- 2005-01-20 US US10/586,494 patent/US7718815B2/en not_active Expired - Lifetime
- 2005-01-20 KR KR1020067014655A patent/KR101310882B1/ko not_active Expired - Lifetime
- 2005-01-20 CA CA002554047A patent/CA2554047A1/fr not_active Abandoned
- 2005-01-20 JP JP2006550030A patent/JP2007518763A/ja active Pending
- 2005-01-20 BR BRPI0506970A patent/BRPI0506970B8/pt not_active IP Right Cessation
- 2005-01-20 RU RU2006126346/04A patent/RU2395504C2/ru active
2006
- 2006-07-20 IL IL176968A patent/IL176968A/en active IP Right Grant
- 2006-07-20 NO NO20063368A patent/NO20063368L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
US20080132567A1 (en)	2008-06-05
NZ548638A (en)	2010-02-26
JP2007518763A (ja)	2007-07-12
BRPI0506970A (pt)	2007-07-03
EP1557166A1 (fr)	2005-07-27
CN1956714A (zh)	2007-05-02
PL380825A1 (pl)	2007-03-19
AU2005205903A1 (en)	2005-08-04
KR20070007776A (ko)	2007-01-16
IL176968A0 (en)	2006-12-10
CN100584323C (zh)	2010-01-27
HK1103282A1 (zh)	2007-12-14
BRPI0506970B1 (pt)	2019-08-13
NO20063368L (no)	2006-10-12
KR101310882B1 (ko)	2013-09-25
WO2005070405A1 (fr)	2005-08-04
IL176968A (en)	2012-10-31
AU2005205903B2 (en)	2010-04-29
RU2006126346A (ru)	2008-01-27
RU2395504C2 (ru)	2010-07-27
US7718815B2 (en)	2010-05-18
BRPI0506970B8 (pt)	2021-05-25

Legal Events

Date	Code	Title	Description
2011-01-20	FZDE	Discontinued

Publication	Publication Date	Title
US7718815B2 (en)	2010-05-18	Alpha-aminoamide derivatives useful in the treatment of lower urinary tract disorders
RU2152786C2 (ru)	2000-07-20	Средство для лечения недержания мочи
JP4410930B2 (ja)	2010-02-10	鎮痛薬として有用なα−アミノアミド誘導体
CA2398199A1 (fr)	2001-08-02	Nouveaux agents therapeutiques utilisant un agoniste .beta.3
US20100016440A1 (en)	2010-01-21	Alpha-aminoamide derivatives useful as anti-inflammatory agents
EP1588704A1 (fr)	2005-10-26	Dérivés d'alpha-aminoamides utiles dans le traitement de l'acroparesthésie nocturne et des troubles de toxicomanie
KR20050094852A (ko)	2005-09-28	항편두통제로 유용한 알파-아미노아미드 유도체
WO1997031637A1 (fr)	1997-09-04	Utilisation d'antagonistes des recepteurs 5-ht1a pour le traitement de l'incontinence urinaire
AU2006275824B2 (en)	2010-12-16	Method of improving wakefulness
MXPA06008188A (en)	2007-04-10	Alpha-aminoamide derivatives useful in the treatment of lower urinary tract disorders
CN1930123B (zh)	2010-06-23	用于预防或治疗伴有神经障碍的膀胱过度活动症的医药组合物
HK1103282B (en)	2010-10-08	Alpha-aminoamide derivatives useful in the treatment of lower urinary tract disorders
MXPA06002189A (en)	2007-04-10	Alpha-aminoamide derivatives useful as anti-inflammatory agents
CA2561293C (fr)	2008-03-18	Traitement de l'incontinence
HK1013799B (en)	2002-02-08	Use of venlafaxine or of an aryloxy propanamine compound for the manufacture of a medicament for the treatment of urinary incontinence